Process for applying crease resistant finishes to cellulosic fabrics and products thereof



' 3,043,719 PROCESS FOR APPLYING GREASE RESISTANT FINISHES TO CELLULOSICFABRICS AND PRODUCTS THEREOF Francis K. Burr, Danvers, and Joseph S.Panto, Dover,

Mass, assignors to United Merchants and Manufacturers, Inc., New York,N.Y., a corporation of Delaware No Drawing. Filed Aug. 19, 1960, Ser.No. 50,606

7 Claims. (Cl. 117-139.4)

increase or improve the crease resistant properties or values incidentto cloth of the character of fabric described without, however, undulytendering or weakening the material.

According to the present invention, there i contemplated a method orprocess for applying resins, especially synthetic cellulose reactantresins and also thermosetting resinous compositions, to fabrics of thecharacter delineated above, such that resin add-onslin amounts equaltowhat We may term, for convenience, the standard or customary quantitieswill produce or give higher crease resistance. A further object of theinvention is, as by way of corollary, a method or process for obtainingcrease resistant values that are substantially equal to conventionalreadings, but which are obtained with lessresin add-ons than normally orcustomarily would be required to get such results. The invention, ofcourse, contemplates also the product of such treatment, namely, fabricsexhibiting or having improved crease resistance as a result of theapplication of crease resistant compositions according to the methodhereinafter described.

Another object of the invention is a method for finishing fabrics inrelation to obtaining crease resistance therein whereby lower quantitiesof resin may be utilized efiiciently to do the crease resisting work ofnormally greater concentrations of resinous material, albeit Withoutunduly tendering or adversely aifecting the strength of the treatedcloth or material.

The term crease resistance as used herein, which is sometimes otherwiselabelled crush resistance or wrinkle resistance, comprehends thatproperty in a fabric which enables it to resist wrinkling or mussing. Adurable crease resistance treatment for a fabric will cause wrinklestherein to disappear or to come out immediately after hanging a shorttime.

The term no iron or non-ironing fabric means a cloth or an article ofapparel made therefrom which previously has been given a treatment torender it crease resistant, so that after normal Wear or usage thegarment thus treated may be washed and hung up to dry, and after dryingwill he in satisfactory condition Without ironing for wearing again. Inplain terms, crease resistance or crease recovery of fabrics means theloss or absence of wrinkles.

The present invention comprises, in its simplest terms, running thecloth through a reaction mixture or bath containing -a reactant resin orprecondensate, or a thermosetting or thermosettable synthetic resincomponent in a solution comprising an aliphatic ketone solvent selectedfrom the class consisting of acetone and methyl ethyl ketone. Accordingto normal practice, fabrics of the character described are given acrease resistant'finish by running the same through a bath containing asolution consisting essentially of a cellulose reactant, or :a heathardenable resin, such as urea formaldehyde resin or melamineformaldehyde resin, a delayed' action catalyst such as the metal saltcatalysts and the amine hydrochloride types and/or diammonium hydrogenphosphate, or di-basic ammonium phosphate, the thermoset resin andcatalyst,

with or without an accompanying softener, being prepared together in amix comprising an aqueous solution so that a typical crease resistantfinish according to normal practice is made up of an aqueous solutioncomprising the urea formaldehyde and/or other resin or reactant materialresin, the delayed acting catalyst, and the balance water.

According to the present invention, however, we have found that byreplacing all or a major part, and preferably most of the water in such.crease resistant finishing solutions with another solvent, viz. analiphatic ketone selected from the class of ketones consisting ofacetone and methyl ethyl ketone, and subsequently hardening orpolymerizing the resin in situ, results are obtained in terms of creaseresistant values which are improved over those normally acquired by theapplication of conventional aqueous resin treating solutions such asthose just described. In fact, the substitution of an organic solventsuch as acetone for water as the solvent in the application ofthermosetting synthetic resinous materials to textiles gives increasedvalues. It will be understood, therefore, that according to the presentmethod a new wash and wear, no-iron finish is obtained which gives thetreated fabric higher than usual wrinkle resistance comprising theapplication of synthetic cellulose reactant or thermosetting resins fromorganic aliphatic ketone solvent solutions to cellulosic fabrics.

Regarding ketone solvents other than those mentioned above, namely,acetone or dimethyl ketone,. and methyl ethyl ketone, it appears thathigher molecular Weight ketones do not have sufiicient tolerance forwater to allow solubility of catalyst materials or to include the Waterportions added to the system, .either directly or by reason of thatwhich occurs in the resin product.

Among the properties and effects obtainable by the instant invention areincreased crease resistance without undue tendering, the production of asatisfactory wash and wear finish, better deposition of the syntheticresin particles on the fabrics treated thereby, and a decrease in thenormal amount of swelling action that usually occurs I upon thedeposition of reactant or heat hardenable synthetic resin solutions,especially those of relatively high Water concentration. Further,according to the present invention, in view of the greater volatility ofthe substitute solvents, it is practical simultaneously to dry and curethe cloth'after impregnation thereof with the crease resistant finishingagent contemplated thereby.

Another interesting facet of the invention is that formulations of thepresent crease resistant finishing agents offer a very convenient anduseful means for the householder or garment wearer, as for example, ahousewife, to apply the same to a garment in much the same manner asstarch is applied before ironing, the excessbeing removed by wringing orspinning in a washing machine. The present compositions and methods ofappiioation should valso be useful to garment manufacturers, tolaundries, and to dry cleaners for wash and wear finishing of garments.For example, a cotton shirt was dipped in a bath containing the presentcrease resistant finish or composition, and thereafter the shirt washand washed and drip dried more than 40 times, and was Worn about 60times, without ever having been re-ironed. A performance of this typeobviously exceeds that of ordinary commercially produced Wash and wearfinishes in shirts that are now on the market.

-The treating solutions ordinarily are prepared simply by mixingtogether an organic solvent solution comprising an aliphatic ketone,preferably acetone, synthetic thermosettable resin, or a reactant orcross-linking pre condensate, preferably a dimethylol ethylene urearesin hereinafter called DMEU, and a suitable catalyst, that is, adelayed acting catalyst such as an amino-propinol hydrochloride known asCatalyst AC. and sold by the Monsanto Chemical Company. A typical resinmix formulation is as follows:

, Grams DMEU resin 100 A.C. Catalyst 10 Water 178 Acetone 712 asa triazone or a triazine or a methylated methylol or an unmethylatedmethylol melamine formaldehyde resin, or urea formaldehyde resin ormixtures or combinations thereofeit-her with each other or with the DMEUresin.v

In place of the Catalyst A.C., any other delayed action catalyst adaptedto promote condensation of the precondensate synthetic resinous materialmay be used, such as the catalyst diammonium phosphate, or a metal saltcatalyst such as zinc nitrate, or magnesium chloride, or

the ethanol-amine hydrochlorides.

The amount of DMEU or other resin ofv the character described may bevaried from about 2% to about 20% by Weight of the treating solution. Atconcentrations below this range the solution has decreased effects,while above 20% no Worthwhile improvements result. The preferredconcentration for the resin is about 10% by weight. The acetone solventor other organic solvent making up the major component of the resinoussolution may be present in amounts ranging from about 50% by weight toabout 90% or 95% by weight of the total treating solution, the preferredconcentration thereof being of the order of about 71% by weight. For thecatalyst there may be used concentrations of the order of from about .5%to about 10% by weight, the, preferred catalyst concentration beingabout 1%. The amount of water is not critical and may range from toabout 35% by weight concentration, the preferred proportion being about18% by weight.

In its simplest terms, according to the present invention the process ofimparting improved crease resistance to cellulosic fabrics involvesrunning the cloth through a reaction mixture or bath containing theseveral resin mix components thus described, namely, the heat settingsynthetic resin precondensate, the organic solvent, and the catalyst.The cloth ordinarily is passed through a bath or solution containingthese components, and after emerging therefrom the excess solution isremoved from the fabric as by passing it through a padder, the clothpicking up from about 50% to about usually about 55% of its weight ofthe treating solution. The treated fabric is then quickly dried, as forexample, on a bank of steam heated drying cans, then cured in a heatingoven at the usual temperatures and times, say for example, for 5 minutesat about 300 F.; the drying time and temperature preceding the curingmay, for example, comprise about 1 minute at about 240 F. It is to beunderstood, of course, that with respect to drying and curing, the timeand temperature are correlative factors and Wide variations in each areto be expected and will be entirely compatible with variations inoperating conditions and equipment, and also variations in the natureand construction of the cloth being treated for crease resistance.

With regard to after-treatment, it will also be understood that manyvariations depending on specification and circumstances may be included.In some cases it is desirable and required to after-Wash. In others, itwill not be necessary to do so. In addition, it may be required that thecloth, after first being impregnated for crease resistance with atreating composition according to the teachings hereof, may subsequentlybe run through a caustic application range, with or without framing, forthe production of a plisse or puckered appearance or other surfacetexture effects. In any case, it is to be understood that theapplication of the present crease resistant finish does not in any Wiserestrict or limit the subsequent treatment of the cloth.

The following examples illustrate the improved crease resistant valuesobtained by the present invention. In all of these examples, theconcentrations recited therein are the solution concentrations and notthe concentration of material on the fabric, and the pick-up from watersolutions is about in every case. In contrast, the pick-up from acetoneand methyl ethyl ketone solutions was about 55% in every case.Therefore, in Examples 1 through 11 following, in those instances wherethe Monsanto crease angles are the same or approximately the same withrespect to fabrics treated with acetone or methyl ethyl ketone solutionsas for fabrics treated "with Water solutions, there is, notwithstanding,an indicated advantage for the acetone or methyl ethyl ketone processbecause about 15% or 20% less resin solids exist on such fabrics aftertreatment. The crease resistance readings were determined on theMonsanto crease angle tester. This is a special device developed byMonsanto Chemical Company for this specific test. Samples of cloth, 1cent. x 4 cent, are cut from the cloth and a fold is made across thelong direction. This fold is placed under a standard "weight, which isgenerally 1 1b., for a period of 5 minutes. The sample is then removedfrom beneath the weight and placed in a clip on the machine and the foldallowed to open. The angle to which it recovers after 5 minutes ismeasured and recorded. This is the so-called crease angle. In reality itis the angle of recovery from creasing.

EXAMPLE 1 The table below serves to contrast the relative superiority ofacetone solvent treating solutions of several or varying concentrationsover conventional water solutions.

Cotton fabric Crease Crease Treatment applied 1 Solvent angle angle warpfilling Ends Picks 80 80 DMEU resin product, 1% A.C. cat 100% acetone137 134 80 80 do 90% acetone/10% 1 120.. 140 139 80 80 80% acetone/% H O142 139 80 80 70% acetone/% H2O" 140 136 80 80 acetone/40% H2O 138 13580 80 100% H20 130 128 80 80 132 128 80 80 ...do 132 131 80 80 do dn 129130 80 80 Control-No treatment 59 I All samples dried at 240 F. for 1min. and cured at 300 F. for 5 min.

EXAMPLE 2 EXAMPLE 4 Example 2 illustrates, as seen below, certainincreased values in crease angles that are obtained by giving thetreated cloth a final washing, or after-washing the fabric 20 dimethylolethylene urea.

The table of figures here given concerns the effects of increasing theconcentration of the resin precondensate Cotton fabric Crease CreaseTreatment applied Acetone content of angle angle solvent (balance water)warp filling Ends Picks 80 6% DMEU product, 1% cat. A.C..-. 80% acetoneunwashed 128 123 80 7 80 do 80% acetone washed 133 134 80 80 7% DMEUproduct, 1% cat. A.C.. 80% acetone unwashed 134 126 80 80 o 80%acetonewashed 137 130 80 80 8% DMEU product, 1% cat. A.C..-- 80%-acetoneunwashed 132 131 80 80 do 80% acetone washed a. 139 141 80 80 9% DMEUproduct, 1% cat. A.C..-. 80% acetone unwashed- 137 134 80 80 -do 4. 80%acetone washed 142 140 80 80 15% DMEU product, 1% cat. A.C. 80% acetoneunwashed. 149 145 80 80 a do 80% acetone washed 154 153 80 80 10% DMEUproduct, 1% cat. A. O. 80% acetone unwashed; 141 140 80 80 ..do 80%acetone washed 142 145 80 80 water unwashed 129 128 80 80 100% waterwashed 135 138 1 Soap at F.

treating solutions.

EXAMPLE 5 In this exampleare shown the results obtained by substitutingother solvents, namely, methyl ethyl ketone and dioxane for the acetoneof the previous examples, and

Cotton fabric Crease Crease Treatment applied Solvent angle angle warpfilling Ends Picks 80 80 10% DMEU resin product, 1% (A.C.) cat 007acetone/10% H2O 140 133 80 80 do 90 a acetone washed 145 141 80 80 80%acetone/20% H30 139 134 80 80 80% acetone washed. 158 144 80 80 20 12280 80 100% H20 washed 131 139 EXAMPLE 3 The readings appearing belowfurnish indications of the relative effect, in terms of creaseresistance, of acetone treating solutions of varying. concentrations,diiferent values being obtained at each concentration for treatedfabrics subsequently given a final wash at both 105 F.

and 160 F.

Cotton fabric I Crease Crease Treatment applied Acetone content ofsolvent angle angle (balance water) warp filling Ends Picks 10 DMEUresin roduct, 1 A.C. cat 907 acetone 139 137 ...%do p 90% acetone washed105 144 141 90% acetone washed 160 F 143 139 ooococcooooeoooooo onoooooooomocooooocoooooo 000000000000 85% acetone 137 137 85% acetonewashed 105 F. 134 136 85% acetone washed 160 F 139 133 75% acetone 139139 75% acetone washed 105 F- 139 134 75% acetone washed 160 F. 145 14080% flfiefnnp 134 131 80% acetone washed 105 F. 136 138 80% acetonewashed 160 F 142 145 the acetone, methyl ethyl ketone, and dioxaneconcentrations are as indicated below, thebalance being water.

resin concentration than had been practised elsewhere, that is, in thepreceding examples.

where the :cotton fabric employed, although of the same. 55

construction, had not been pretreated with the sodium 'borohydride.Furthermore, the treatment indicated by Cotton Fabric Grease CreaseTreatment applied angle angle warp filling Cotton -Ends Pl\S fabricCrease Crease V V Treatment appll angle angle 80 80 10% DMEU 1% catalystUnwashed 140 144 Warp, fil 80% A.C. Ends Picks 10 8O 80 Wasbed 150 145 ad is lit 8 O 3S 9 80 80 807 acetone Unwashed 129 135 EU h 4 4 0 80Washed H 0 D1 140 131 80 80 10g8%D1vli/1EK.1% catalyst Unwas ed 1 6 1 880 8O Washed-Soap '136 136 d 153 1 3 80 S0 t0ne UHWaShGd 145 147 80 80Unwashed 150 154 28 i3 556 353E133 iig iii 15 e-mews o g" ti' t'a 2i i1' 5" so so 100 7;7 water .do 129 12s 80 80 g M E i was B 300 g.Acetone. 80 80 do Washed". 155 153 0 EXAMPLE 7 EXAMPLE 6 p In theschedule appearing below are seen comparative results in terms of creaseresistance properties of cotton I In this example is Seen theSuitability f employing i cloth of the same type and construction asthat used in all tures of 'ke'tones, as for example, a mixture ofdimethyl Qther pl'ewouS examples namely 9 X 80 cotton Pnnt ketone oracetone, and methyl ethyl ketonein the resin s a i g g z g f s treatingbath, with figures being given to cover specific 6 10 t at d g g t qapplications of both Washed and unwashed treated mate- L s eXamP e f p omg are rial It should be mentioned that the crease resistance tel-88mg.the purpose of Snowmg rephcates of data vah'le n b Xam 1 a t 1illustrating improvement ofthe acetone solvent system 6 b1 i p e no Irey or over straight water. The figures in the left-hand column y P 6Crease reslstance gures or U in inches, in both examples, refer to thewidth of the Valli glven the j F examples hereof 'bficause fabric beforestarting the trials, and these readings were the cotton fabnf: thlsexamRle hadfbeen Elven 3 taken as part of another investigation havingto do with Pretreatment Wlth Sodlllm bofohydrlde Whlch alters the fabricshrinkage and in that respect unrelated to the presefiect Produced,glvmg SOmeWhat-msher crease reslstance 35 cut work. This explains thereason for setting forth the values than were obtained in theother casesor examples multiple results.

Treatment applied Crease Crease Fabric, angle angle inches warp fillingSolvent 35% 10% resin, 1% cat 100% HiO,n0t pre-dried,cured Unwashed 13335% do do Washed 37% Unwashed. 128 131 37% Washed 134 131 39 Unwashed133 131 39 Washed 128 133 35V Unwashed" 139 35% Woshed- 141 13s 37%Unwashed 140 141 37% Washed 146 144 39 Unwashed 138 139 39 Washed 142138 EXAMPLE 8 In Example 8 the same type of cotton cloth as that ofprevious examples is subjected to acetone and aqueous treatingsolutions, the procedure of Example 7 being modizfied in that in thepresent example the cloth was pre-dried prior to curing.

Treatment applied Crease Crease Fabric, angle angle inches warp fillingSolvent 35% 10% DMEU, 1% cat 80% aeietone, 20% H20, pre-dried, Unwashed139 135 cure 35% Washed 138 139 37% Unwashed 137 134 37% Washed".-. 137139 39 Unwashed 137 139 39 Washed 139 137 35% Unwashed 128 129 35%Washed 131 133 3 /6 Unwashed 129 133 37% Washed... 131 133 39 Unwashed--127 131 39 Washed 129 130 EXAMPLE 9 In Example 9, additional readings ofcrease resistance values for 80x 80 cotton cloth fabric are given, whichwere obtained by subjecting cloth to 10% DMEU acetone solutions and 10%DMEU water solutions.

80 x 80 cotton fabric Monsanto crease angles Washed Unwashed SolventWarp Filling Warp Filling 10% DMEU 80% acetone-% 120-. 129. 0 130. 0128. 6 130. 0 Do 2 .1135 120.0 113.0 117.3 130 +80% acetone-20% 1140--130.5 132.1 127.1 130.0 Do 2 122.3 123.1 122.1 126.3 D0 +30% acetone-20%H20" 135. 5 143. 0 134. 0 133. 0 D0 do 136.3 140.5 133.6 132.6 20 Do+1120 128.8 125.1 125.0 130.3

EXAMPLE 10 Example 10 illustrates the effects of the application ofaqueous and acetone treating solutions on a cellulosic material or clothother than cotton, namely, a 100% regenerated cellulose spun rayonusually described as butcher linen, In each treating solution, the samecatalyst was used as in the preceding examples, its concentration beingtypical, viz. 10% on the weight of the DMEU resin.

Monsanto crease angles Blue rayon Solvent Washed Unwashed Warp FillingWarp Filling 20% DMEU. 110.8 118.5 130.6 120.0 15% DMEU. 99.8 120.1126.0 40 10% DMEU. +1110. 94.6 96.0 110.0 113.0 20% DMEU. +5127 acetoneand 20% 131.6 123.3 141.1 145.6

2 15% DMEU. do 115.0 116.0 123.0 120.0 10% DMEU- do 103.5 109.8 117.3118.5

REPEAT 20% DMEU. 124.8 129.6 131.1 15% DMEU. 119.3 126.4 122.3 10% DMEU-115.8 110.6 120.3 20% DMEU- 133.1 140.0 140.1 15% DMEU do 129.1 130.0135.0 138.8 10% DMEIL 1 do 116.1 118.0 119.0 113.0

EXAMPLE 11 In the table below, other resins are substituted fordimethylol ethylene urea, viz.: Aerotex 23, which is a combination ofTriazone and urea formaldehyde resins of American Cyanamid; ResiponN.D.C., which is a modified urea formaldehyde resin of the ArkansasChemical Company; and Rhonite D5, which is also a modified U.F. resin,made and sold by Rohm & Haas. D.A. Catalyst is a solution of zincnitrate; and MX Catalyst is a magnesium chloride catalyst sold byAmerican Cyanamid. Although the concentrations of the several solutioncomponents are set forth differently in this table than was the case inthe preceding examples, nevertheless, in every instance of the acetonesystem treatments, 0f the 75 solvent is acetone. Moreover, we mentionhere again that the pick-up in the case of acetone treating solutions isabout 55%, whereas it is about 70% in the case of water solutions.Because of this circumstance where acetone and water readings in thistable are alike, or nearly alike, nevertheless such readings trulyindicate a higher efiiciency for the resin applied from acetone systemsbecause less resin accomplishes the same result.

Monsanto crease angles Washed Unwashed Warp Filling Warp Filling 850 cc.acetone plus 170 cc. H20, 120 g.

Aerotex 23, 30 g. MX Catalyst 128. 5 129. 0 131.3 130. 1. 850 cc. H20,120 g. Aerotex 23, 30 g.

MX Catalyst 136. 8 136. 6 131. 4 131.3 780 cc. 1120, 200 g. ResiponN.D.G.,

50 g. Cat. D.A 145.0 143.1 133. 8 137. 3 780 cc. acetone, 156 cc. H20,200 g.

Resipon N.D.C., 50 g. Cat. D.A-. 150. 3 149.3 142. 5 142.0 780 cc. H20,200 g. Rhonite-D-5, 50

g. Cat. D.A 144. 5 143.5 142. 147. 780 cc. acetone, 156 cc. 1120, 200 g.Rhouite D-5, 50 g. Oat. D.A 149. 8 148.4 140. 143.3

Table I, hereunder, gives additional examples and data concerning theapplication of the present invention to cotton fabrics wherein aldehyde,namely, formaldehyde, replaces the resin in the treating bath.

In Table II, examples are given of the application of urea formaldehydeand melamine formaldehyde resin treating solutions to cotton.

In Table III, rayon fabrics are treated with urea formaldehyde, melamineformaldehyde, and dimethylol ethylene urea formaldehyde solutions.

Table IV contains illustrations of the application of the invention tolinens, as by resin impregnating agents comprising dimethylol ethyleneurea formaldehyde, melamine formaldehyde, and urea formaldehyde.

In these four tables numbered I, II, III, and IV, the treatment islisted in percentage based on the weight of the solution, and it will beunderstood that these are not the percentages of materials on thefabric. The pick-up from water solution is approximately 70%, and about55% in the case of the ketone or acetone systems. For that reason, eventhough in some cases set down in these four tables, the crease anglesare not appreciably different between the water and acetone systems,nevertheless, the

results are significant when it is considered that there isapproximately 15%; less pick-up of resin in the case of the ketonesystems.

Several additional comments about the data set forth in Tables I, II,III, and IV should also be made, as follows. Curing was always practisedat 300 F, unless stated otherwise. The concentration of formaldehyde islisted as formaldehyde, although actually what was used was the regular37% concentration material which is now quite generally furnishedcommercially. In all cases the catalyst used was anamino-propanol-hydrochloride, such as. the catalyst known as CatalystA.C., previously mentioned herein.

The urea formaldehyde resin used in these four tables was a typicalpaste resin; the Resloom M-75 is a methylated methylol melamineytheResloom HP is an unmethylated methylol melamine; and the Resloom E-6 3is a special new resin manufactured by Monsanto Chemical Company, thenature of which is not presently known 1.1 to the applicant. However,the Resloorn E-63 is in the general category of the Resipon NDC ofArkansas mentioned above, and also the Aerotex 23 Special of AmericanCyanamid, also previously mentioned.

Table I FORMALDEHYDE ON 80 x 80 COTTON Monsanto crease angle Treatment,percent weight of solution Unwashed Washed Notes W F W F 5%Formaldehyde, 124 129 ,Oured at 350 F.

1% catalyst, 80% acetone, 14% water. 10% formaldehyde, 137 142 Do.

2% catalyst, 80%

acetone, 8% water. 7 2O 5% formaldehyde, 1% 119 119 Do.

catalyst, 94% Water. 10%formaldehydc, 2% 130 135 Do.

catalyst, 88% water.

formaldehyde, 139 144 Do. 2.5% catalyst, 77.5% water.

5% formaldehyde, 2% 108 111 107 107 Reg. cure (300 F.).

catalyst, 93% water. 5% formaldehyde, 2% 123 126 123 124 Do.

catalyst, 84% acetone, 9% water.

Table II SPECIAL RESINS ON 80 x 80 COTTON Monsanto crease angleTreatment, percent weight of solution Unwashed Washed W F W F 40 10%Resloom E-63, 0.5% catalyst, 89.5% p Water 123 123 118 119 10% ResloomE453, 0.5% catalyst, 72% acetone, 17.5% water 127 125 129 129 10%Resloom H.P., 1% catalyst, 89% water- 120 125 119 124 10% Resloom H.P.,1% catalyst, 71.2% acetone, 17.8% Water 124 128 126 125 10% ResloomM-75, 1% catalyst, 89% Water 118 122 120 123 10% Resloorn M-75, 1%catalyst, 71.2% acetone, 17.8% Water 118 120 121 120 20% Resloom M-75,2% catalyst, 78% water.. 130 131 129 138 20% Resloom M75, 2% catalyst,62.4%acetone, 15.6% Water 141 141 142 143 20% Urea Formaldehyde, 2%catalyst, 78%

Water no 117 113 122 20% Urea Formaldehyde, 2% catalyst, 62.4%

acetone, 15.6% Water 121 118 120 120 Table III RESIN TREATMENT on nnYoNMonsanto crease angle Treatment, percent weight of solution UnwashedWashed W F W F.

20% urea formaldehyde, 2% catalyst, 78%

water 120 121 115 120 6, 20% urea formaldehyde, 2% catalyst, 62%

acetone, 16% water 127 130 126 126 20% DMEU, 2% catalyst, 78% Water 1115 117 115 115 20% DMEU, 2% catalyst, 60.2% acetone,

17.8% water 129 128 127 126 20% Resloom M-75, 2% catalyst, 78% water 102104 99 101 20% Besloom M-75, 2% catalyst, 60.2% acetone, 17.8% Water 122121 123 116 Table I V RESIN TREATMENTS ON LINEN Monsanto crease angleTreatment, percent weight of solution Unwashed Washed W F W F 20% DMEU,2% catalyst, 78% Water 108 109 102 110 20% DMEU, 2% catalyst, 60.2%acetone,

17.8% Water 139 130 118 126 14% urea formaldehyde, 1% catalyst,

water 105 105 103 14% urea formaldehyde, 1% catalyst, 68%

acetone, 17% Water 102 115 107 20% urea formaldehyde, 2% catalyst, 78%

water 112 103 107 101 20% urea formaldehyde, 2% catalyst, 02%

acetone, 16% water 112 112 100 20% Rcslooin M-75, 2% catalyst, 78% Water111 115 100 104 20% Resloom M-75, 2% catalyst, 62.4% acetone, 15.0%water .1 113 119 118 121 In the light of the foregoing, the following isclaimed:

1. Method of improving the wash and wear and crease resistanceproperties of cellulosic fabrics, which includes the steps ofimpregnating the same With reactant precondensate material selected fromthe class of cellulose reacting materials consisting of ureaformaldehyde, melamine formaldehyde, dimethylol ethylene urea,formaldehyde, triazones, and triazines, dissolved in an impregnatingsolution comprising a major proportion of an aliphatic ketone solventand a minor proportion of water, and subsequently insolubilizing theprecondensate in situ.

' 2. The method of claim 1 in which the aliphatic ketone solvent isacetone. 1

3. The method of claim 1 in which the aliphatic ketone solvent is methylethyl ketone.

4. The method of claim 1 in which the ketone solvent consists of amixture of acetone and methyl ethyl ketone.

5. Method of improving the Wash and wear and crease resistanceproperties of cellulosic fabrics, which includes thesteps ofimpregnating the same with reactant precondensate material selected fromthe class of cellulose reacting materials melamine formaldehyde,dimethylol ethylene urea, formaldehyde, triazones, and triazines,dissolved in an impregnating solution comprising a major proportion of adioxane solvent and a minor proportion of water, and

subsequently insolubilizing the precondensate in situ.

6. Method of improving the wash and wear and crease resistanceproperties of cellulosic fabrics, which includes the steps ofimpregnating the same with reactant precondensate material selected fromthe class of cellulose reacting materials consisting of ureaformaldehyde, melamine formaldehyde, dimethylol ethylene urea,formaldehyde, triazones, and triazines, dissolved in an impregnatingsolution comprising a major proportion of an acetic anhydride solventand a minor proportion of water, and subsequently insolubilizing theprecondensate in situ. i

7. Method of improving the wash and Wear and crease resistanceproperties of cellulosic fabrics, which includes the step ofimpregnating the same with reactant precondensate material, namely,formaldehyde, dissolved in an impregnating solution comprising a majorproportion of an aliphatic ketone solvent and a minor proportion ofWater.

References Cited in the file of this patent UNITED STATES PATENTS2,888,369 Ratclifie et al May 26, 1959 consisting of urea formaldehyde,

1. METHOD OF IMPROVING THE WASH AND WEAR AND CREASE RESISTANCEPROPERTIES OF CELLULOSIC FABRICS, WHICH INCLUDES THE STEPS OFIMPREGNATING THE SAME WITH REACTANT PRECONDENSATE MATERIAL SELECTED FROMTHE CLASS OF CELLULOSE REACTING MATERIALS CONSISTING OF UREAFORMALDEHYDE, MELAMINE FORMALDEHYDE, DIMETHYLOL ETHYLENE UREA,FORMALDEHYDE, TRIAZONES, AND TRIAZINES, DISSOLVED IN AN IMPREGNATINGSOLUTION COMPRISING MAJOR PROPORTION OF AN ALIPHATIC KETONE SOLVENT ANDA MINOR PROPORTION OF WATER, AND SUBSEQUENTLY INSOLUBILIZING THEPRECONDENSATE IN SITU.